Nitrogen-containing heterocyclic epoxy curing agents, compositions and methods

Abstract

Amine-epoxy curing agents are disclosed including at least one saturated heterocyclic compound having two nitrogen heteroatoms according to formula (I) and at least one saturated fused bicyclic heterocyclic compound having three nitrogen heteroatoms according to formula (II):wherein X is independently selected from a hydrogen atom, a linear or branched C1 to C4 alkyl group and a substituted or un-substituted phenyl group, Y1 is a direct bond or a divalent polyethylene polyamine group having 1 to 8 nitrogen atoms or a divalent polyethylene polyamine derivative having 1 to 8 nitrogen atoms, Y2 is a direct bond or a divalent polyethylene polyamine group having 1 to 7 nitrogen atoms and R is independently a hydrogen atom or a group selected from C1-C8 linear, cyclic, and branched alkyl, alkenyl, and alkaryl groups.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority from U.S. Ser. No. 62 / 256,262 filed Nov. 17, 2015 having the same title, which is incorporated herein by reference in its entirety.BACKGROUND OF THE INVENTION[0002]The present invention is directed to nitrogen-containing heterocyclic epoxy curing agents, compositions, and methods.[0003]Epoxies are known for their excellent adhesion, chemical and heat resistance. In addition they also have good-to-excellent mechanical properties, and good electrical insulating properties. Cured epoxy resin systems are found in an extensive range of applications within the coatings, adhesives, and composites markets. Specific examples include epoxy composite using carbon fiber and fiberglass reinforcements, structural adhesives, protective coatings for metal surface, and construction products for concrete, cementitious or ceramic substrates, often referred to as civil engineering applications such as formulations for concret...

AI Technical Summary

Benefits of technology

The amine-epoxy curing agent described in this patent has improved compatibility with epoxy resin, leading to faster and more complete curing. It also results in less yellowing of the epoxy cured with it.

Problems solved by technology

However, many epoxy coatings suffer from slow cure at low application temperatures (≦5° C.) and a common side effect of the slow cure is that coatings can develop poor surface defects and a greasy surface appearance referred to as blushing, carbamation of or water spotting.

These problems are in part attributed to the slow amine-epoxy reaction rate and partial incompatibility between the amine curing agent and epoxy resin.

This results in incomplete amine-epoxy reaction and insufficient crosslinking which can lead to poor physical properties and poor coating performance.

If free amine is present on the surface for too long a period, then the amine will react with water and carbon dioxide in the atmosphere and develop a white film on the surface which can lead to poor coating performance.

Another problem is that the cure requires longer time for coating to set and dry, which means longer time to return to service or for the subsequent layer to be over coated.

However, incorporation of these species can only be used at low levels since they can cause the epoxy resin to homopolymerize and the resultant system to become brittle.

Also they have a significant impact in causing the final epoxy system in be more prone to yellowing.

However, many of the curing agents used today providing high reactivity have drawbacks, which are either technical, such as uncontrolled reactivity, where a severe exotherm can result in damaging component parts during production as well as leading strong yellowing, in addition there are also health and safety concerns, where many materials may exhibit high vapor pressure and / or toxic labeling.

A significant issue with this application is the presence of DETA, which is coming under regulatory pressure because of health and safety aspects.

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